ot very funny, but interesting history. Cholos used to wear pressed blue jeans with glaringly white tee shirts. The style derived from prison garb. Many of the people they admired spent time there. The droopy drawer look comes from a little closer to home. Short term jail inmates often have their clothes confiscated, especiall if they're dirty, The replacements usually come from a rag bag of available old clothes. Smart jailers make sure ensure that the new clothes discourage vigorous activity. Jail fashion. Source? This came froms a local newspaper article, citing the sheriff's office and a sociologist.